Silicon Compounds for Organic Synthesis

Silicon as an element belongs to Group IV of the Periodic Table and thus has properties similar to carbon. A silicon atom can form a σ-bond to a carbon atom and thereby form a variety of organic silicon compounds. However, as carbon belongs to period II and silicon to period III, the two element's atoms differ in atomic size, ionization energy, electronegativity, and atomic orbital configuration amongst other things. These differences cause organic silicon compounds to exhibit characteristic reactivities that are not found in carbon compounds. Silylenol ethers, hydrosilanes, Peterson type reagents, silylcyanides, silyldiazomethane and others are increasingly being used in organic syntheses, not only for their protective moieties, but also as reagents of general interest.

B1769 B1769 F0518 F0518 B1695 B1695
T1510 T1510 T1498 T1498 B1892 B1892
C1370 C1370 C1402 C1402 C0862 C0862
I0449 I0449 P1172 P1172 T1570 T1570
T1579 T1579 H0089 H0089 B1688 B1688
B1699 B1699 B1768 B1768 D2144 D2144
T2467 T2467 D1608 D1608 B1298 B1298
T1123 T1123 T2465 T2465 T1556 T1556
T1648 T1648 M0759 M0759 P1280 P1280
C1339 C1339 D2934 D2934 D2935 D2935
T1441 T1441 T1458 T1458 T2089 T2089
T1536 T1536 M1883 M1883 T1514 T1514
T1469 T1469 T1299 T1299 B3047 B3047
T2466 T2466 B1654 B1654 M1884 M1884
T1535 T1535 T1500 T1500 M1885 M1885
M1882 M1882 T1573 T1573 T2284 T2284
A1326 A1326 A0927 A0927 A1858 A1858
A0729 A0729 B2334 B2334 B1856 B1856
B1813 B1813 B2004 B2004 B1302 B1302
B1245 B1245 B1090 B1090 B1857 B1857
B1087 B1087 C1492 C1492 D1147 D1147
C1358 C1358 C1419 C1419 C0306 C0306
C1982 C1982 D2469 D2469 D3135 D3135
D0358 D0358 D2403 D2403 D2262 D2262
D3386 D3386 D1789 D1789 D2196 D2196
D1390 D1390 D1825 D1825 D2406 D2406
D2820 D2820 T1584 T1584 H0638 H0638
H0091 H0091 I0324 I0324 H0915 H0915
M1264 M1264 M1460 M1460 B1103 B1103
B1906 B1906 B0511 B0511 B0830 B0830
T0492 T0492 T0591 T0591 T1277 T1277
B1728 B1728 M1077 M1077 T0590 T0590
T0585 T0585 P1250 P1250 H0893 H0893
S0421 S0421 H0894 H0894 B1436 B1436
B0995 B0995 T1525 T1525 B1223 B1223
B1663 B1663 T0636 T0636 T2043 T2043
M0450 M0450 T0398 T0398 T0407 T0407
T0662 T0662 T1468 T1468 T1689 T1689
T1334 T1334 T1533 T1533 T1078 T1078
T1588 T1588 T0990 T0990 I0308 I0308
T1106 T1106 T0871 T0871 T1684 T1684
T1239 T1239 T0801 T0801 T1146 T1146
T1213 T1213 T1250 T1250 T1184 T1184
T1451 T1451 T0939 T0939 T0661 T0661
P1248 P1248 P1217 P1217 T1463 T1463
T1639 T1639
B1769 (1-Bromovinyl)trimethylsilane
F0518 (1-Fluorovinyl)methyldiphenylsilane
B1695 (2-Bromoallyl)trimethylsilane
T1510 (2-Trimethylsilylethyl)triphenylphosphonium Iodide
T1498 (3-Trimethylsilyl-2-propynyl)triphenylphosphonium Bromide
B1892 (Bromomethyl)trimethylsilane
C1370 (Chloromethyl)dimethylisopropoxysilane
C1402 (Chloromethyl)triethoxysilane
C0862 (Chloromethyl)trimethylsilane
I0449 (Iodomethyl)trimethylsilane
P1172 (Phenylthiomethyl)trimethylsilane
T1570 (Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent]
T1579 (Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent]
H0089 1,1,1,3,3,3-Hexamethyldisilazane
B1688 1,2-Bis(chlorodimethylsilyl)ethane [Protecting Reagent for Primary Amines]
B1699 1,2-Bis(dimethylsilyl)benzene
B1768 1,2-Bis(trimethylsilyloxy)cyclobutene
D2144 1,2-Dichlorotetramethyldisilane
T2467 1,3,5-Tris[4-(trifluoromethanesulfonyloxy)-3-(trimethylsilyl)phenyl]benzene
D1608 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane [Hydroxyl Protecting Agent]
B1298 1,4-Bis(trimethylsilyl)-1,3-butadiyne
T1123 1-(Trimethylsilyl)-1-propyne
T2465 1-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate
T1556 1-(Trimethylsilyloxy)cyclohexene
T1648 1-(Trimethylsilyloxy)cyclopentene
M0759 1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene
P1280 1-Phenyl-1-trimethylsilyloxyethylene
C1339 2-(Chloromethoxy)ethyltrimethylsilane (stabilized with Diisopropylethylamine)
D2934 2-(Dimethylsilyl)pyridine
D2935 2-(Dimethylvinylsilyl)pyridine
T1441 2-(Trimethylsilyl)ethanol
T1458 2-(Trimethylsilyl)ethoxymethyltriphenylphosphonium Chloride
T2089 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate
T1536 2-(Trimethylsilyloxy)furan
M1883 2-Methyl-6-(trimethylsilyl)phenyl Trifluoromethanesulfonate
T1514 2-Trimethylsilyl-1,3-dithiane
T1469 2-Trimethylsilyloxy-1,3-butadiene
T1299 2-Trimethylsilylthiazole
B3047 3,3'-Bis(trimethylsilyl)biphenyl-4,4'-diyl Bis(trifluoromethanesulfonate)
T2466 3-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate
B1654 3-Bromo-1-(trimethylsilyl)-1-propyne
M1884 3-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate
T1535 3-Trimethylsilyl-2-oxazolidinone [Trimethylsilylating Reagent]
T1500 3-Trimethylsilyl-2-propyn-1-ol
M1885 4-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate
M1882 4-Methyl-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate
T1573 4-Trimethylsilyloxy-3-penten-2-one
T2284 5-(Trimethylsilyl)-1,3-cyclopentadiene
A1326 Allyl(chloromethyl)dimethylsilane
A0927 Allyloxytrimethylsilane
A1858 Allyltriisopropylsilane
A0729 Allyltrimethylsilane
B2334 Benzylchlorodimethylsilane
B1856 Benzyltrimethylsilane
B1813 Bis(chloromethyl)dimethylsilane
B2004 Bis(methylthio)(trimethylsilyl)methane
B1302 Bis(trimethylsilyl) Malonate
B1245 Bis(trimethylsilyl) Sulfate
B1090 Bis(trimethylsilyl)acetylene
B1857 Bis(trimethylsilyl)methane
B1087 Bromotrimethylsilane
C1492 Chlorodiisopropylsilane
D1147 Chlorodimethylphenylsilane
C1358 Chloromethyl(dichloro)methylsilane
C1419 Chloromethyldimethylphenylsilane
C0306 Chlorotrimethylsilane
C1982 Cyclohexyl(dimethoxy)methylsilane
D2469 Di-tert-butyldichlorosilane
D3135 Di-tert-butylsilyl Bis(trifluoromethanesulfonate)
D0358 Dichlorodimethylsilane
D2403 Diethoxymethylsilane [Hydrosilylating Reagent]
D2262 Diethylisopropylsilyl Chloride
D3386 Dimethoxymethylvinylsilane
D1789 Dimethylketene Methyl Trimethylsilyl Acetal
D2196 Dimethylphenylsilane
D1390 Diphenylmethylchlorosilane
D1825 Diphenylmethylsilane
D2406 Diphenylsilane
D2820 Diphenylsilane
T1584 Ethyl (Trimethylsilyl)acetate
H0638 Hexamethyldisilane
H0091 Hexamethyldisiloxane
I0324 Isopropenyloxytrimethylsilane [Trimethylsilylating Agent]
H0915 Lithium Hexamethyldisilazide (29% in Tetrahydrofuran, ca. 1.6mol/L)
M1264 Methoxymethyltrimethylsilane
M1460 Methylenebis[dimethyl(2-pyridyl)silane]
B1103 N,N'-Bis(trimethylsilyl)urea
B1906 N,O-Bis(tert-butyldimethylsilyl)acetamide [tert-Butyldimethylsilylating Agent]
B0511 N,O-Bis(trimethylsilyl)acetamide
B0830 N,O-Bis(trimethylsilyl)trifluoroacetamide
T0492 N-(Trimethylsilyl)diethylamine
T0591 N-(Trimethylsilyl)dimethylamine
T1277 N-(Trimethylsilyl)morpholine
B1728 N-Benzyltrimethylsilylamine
M1077 N-Methyl-N,O-bis(trimethylsilyl)hydroxylamine
T0590 N-Trimethylsilylacetamide
T0585 N-Trimethylsilylimidazole
P1250 Phenyl Trimethylsilylmethyl Sulfone
H0893 Potassium Hexamethyldisilazide (11% in Toluene, ca. 0.5mol/L)
S0421 Silicon Tetraisothiocyanate
H0894 Sodium Hexamethyldisilazide (contains 2-Methyl-2-butene) (38% in Tetrahydrofuran, ca. 1.9mol/L)
B1436 tert-Butoxydiphenylchlorosilane (stabilized with CaCO3)
B0995 tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
T1525 tert-Butyldimethylsilyl Trifluoromethanesulfonate
B1223 tert-Butyldiphenylchlorosilane
B1663 tert-Butylmethoxyphenylsilyl Bromide
T0636 Tetrachlorosilane
T2043 Tributylsilane
M0450 Trichloro(methyl)silane
T0398 Trichlorosilane
T0407 Trichlorovinylsilane
T0662 Triethylsilane
T1468 Trifluoromethanesulfonic Acid Diethylisopropylsilyl Ester
T1689 Trifluoromethanesulfonic Acid Triethylsilyl Ester
T1334 Trihexylsilane
T1533 Triisopropylsilane
T1078 Triisopropylsilyl Chloride
T1588 Triisopropylsilyl Trifluoromethanesulfonate
T0990 Trimethylsilyl Cyanide
I0308 Trimethylsilyl Iodide (stabilized with Aluminum)
T1106 Trimethylsilyl Isocyanate
T0871 Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent]
T1684 Trimethylsilylacetic Acid
T1239 Trimethylsilylacetylene
T0801 Trimethylsilylazide
T1146 Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.60mol/L)
T1213 Trimethylsilylmethanethiol
T1250 Trimethylsilylmethanol
T1184 Trimethylsilylmethyl Azide
T1451 Trimethylsilylmethylmagnesium Chloride (20% in Ethyl Ether, ca. 1mol/L)
T0939 Triphenylchlorosilane
T0661 Triphenylsilane
P1248 Tris(trimethylsilyl) Phosphate
P1217 Tris(trimethylsilyl) Phosphite
T1463 Tris(trimethylsilyl)silane (stabilized with TBBP) [Reducing Reagent]
T1639 Tris(trimethylsilyloxy)ethylene

For other silicon compounds and GC derivatizing reagents, please refer to "Chemicals by Class", and "Analytical Chemistry", respectively.

Classes of Silicon Compounds


GC Derivatizing Reagents



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